Title

Tracking the Pathways of Peptoid Fragmentation

Poster Number

16B

Lead Author Major

Biochemistry

Lead Author Status

5th year Senior

Format

Poster Presentation

Faculty Mentor Name

Jianhua Ren

Faculty Mentor Email

jren@pacific.edu

Faculty Mentor Department

Chemistry

Graduate Student Mentor Name

Yadwinder Singh Mann

Graduate Student Mentor Email

y_mann@u.pacific.edu

Graduate Student Mentor Department

Pharm. & Chem. Sciences

Abstract/Artist Statement

In the present investigation, the fragmentation pattern of two isomeric peptoids having neutral residues was compared using mass spectrometry. Being able to understand how peptoids fragment will help to provide more insight in establishing de novo sequences of peptoid libraries. Peptoids resembles peptide in their general structure but are different than the latter because the side chains are attached to a nitrogen instead of an ɑ-carbon. Applications of peptoids in therapeutics, catalysts, molecular machine and possible information storage house in future, etc make them a wonderful synthetic polymer.

For our study, two isomeric peptoid having alternating N-(2-methyloxyethyl)glycine (Nme)and N-(2-phenylethyl)glycine (Npe) with six residues were synthesized using Solid-Phase Peptide Synthesis (SPPS) method. This method allows for the synthesis of peptoids chains sequentially on a resin. The resin is activated for peptoid synthesis by deprotecting the Fmoc group with 20% Piperidine in dimethylformamide (DMF).Peptoid synthesis involves 2 steps: bromoacetylation and displacement. In bromoacetylation, a mixture of diisopropylcarbodiimide (DIC) and bromoacetic acid is used in DMF. In the displacement step, the bromine in the peptoid is displaced with the amine of choice in DMF solution. These bromoacetylation and displacement reactions were repeated until a desired sequence of peptoid was synthesized. After synthesis, the final step involves cleavage and purification. The fragmentation patterns of the peptoids were analyzed using Mass Spectrometry. The SPPS method was shown to be an efficient protocol for peptoid synthesis and resulted in products with high yield. The peptoids were found to follow the same type of fragmentation pattern regardless of the side chain.

After gaining insight on peptoid fragmentation, this knowledge will be used for further examination on how acidic and basic side chains will affect peptoid fragmentation patterns.

Location

DeRosa University Center Ballroom

Start Date

27-4-2018 10:00 AM

End Date

27-4-2018 12:00 PM

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Apr 27th, 10:00 AM Apr 27th, 12:00 PM

Tracking the Pathways of Peptoid Fragmentation

DeRosa University Center Ballroom

In the present investigation, the fragmentation pattern of two isomeric peptoids having neutral residues was compared using mass spectrometry. Being able to understand how peptoids fragment will help to provide more insight in establishing de novo sequences of peptoid libraries. Peptoids resembles peptide in their general structure but are different than the latter because the side chains are attached to a nitrogen instead of an ɑ-carbon. Applications of peptoids in therapeutics, catalysts, molecular machine and possible information storage house in future, etc make them a wonderful synthetic polymer.

For our study, two isomeric peptoid having alternating N-(2-methyloxyethyl)glycine (Nme)and N-(2-phenylethyl)glycine (Npe) with six residues were synthesized using Solid-Phase Peptide Synthesis (SPPS) method. This method allows for the synthesis of peptoids chains sequentially on a resin. The resin is activated for peptoid synthesis by deprotecting the Fmoc group with 20% Piperidine in dimethylformamide (DMF).Peptoid synthesis involves 2 steps: bromoacetylation and displacement. In bromoacetylation, a mixture of diisopropylcarbodiimide (DIC) and bromoacetic acid is used in DMF. In the displacement step, the bromine in the peptoid is displaced with the amine of choice in DMF solution. These bromoacetylation and displacement reactions were repeated until a desired sequence of peptoid was synthesized. After synthesis, the final step involves cleavage and purification. The fragmentation patterns of the peptoids were analyzed using Mass Spectrometry. The SPPS method was shown to be an efficient protocol for peptoid synthesis and resulted in products with high yield. The peptoids were found to follow the same type of fragmentation pattern regardless of the side chain.

After gaining insight on peptoid fragmentation, this knowledge will be used for further examination on how acidic and basic side chains will affect peptoid fragmentation patterns.